Copper-catalyzed intramolecular hydroamination of allenylamines to 3-pyrrolines or 2-alkenylpyrrolidines

Abstract

Copper salts, such as CuCl, CuI, CuCl 2 and Cu(OTf) 2 , were used to catalyze the intramolecular hydroamination of allenylamines to provide the corresponding 3-pyrrolines or 2-alkenylpyrrolidines.Leave this area blank for abstract info.

Enantioselective copper catalysed, direct functionalisation of allenes via allyl copper intermediates

“…In addition to the aforementioned enantioselective processes, there have been reports of the non-enantioselective copper-catalysed functionalisation of allenes that enables access to diversely functionalised molecules that are ripe for the development of enantioselective variants. As well as the silylative variants of the aforementioned borylative couplings of aldehydes, 26 ketones 27 and imines, 21 described above, such copper catalysed functionalisations of allenes include protoboration that selectively delivers alkenyl or allylic boronic esters, 28 borostannylation that yields β-boryl allyl stannanes, 29 hydrocupration followed by branch selective imine allylation, 22 carboboration that produces alkenyl boronic esters, 30 intramolecular hydroamination for the formation of 3-pyrrolines or 2-alkenylpyrrolidines, 31 and conjugate addition type processes of allenoates and their derivatives. 32 …”

Synthesis of Saturated Heterocycles via Metal-Catalyzed Alkene Hydroamination or Hydroalkoxylation Reactions

“…With the recent development of There are reports of other Lewis acidic metal complexes that catalyze the 5-exocyclohydroamination of aminoallenes. For example, aminoallenes such as 116 containing a basic amine readily cyclized to form 2-vinyl-pyrrolidines in the presence of copper or silver salts (Scheme 51) [97]. Copper(II) triflate catalyzes the cyclization of primary aminoallenes (e.g., 118!119) as well as 5-endocyclizations of α-aminoallenes such as 120.…”

Novel Cyclization Reactions of Aminoallenes

“…Both the synthesis of 3‐pyrrolines or 2‐alkenylpyrrolidines through copper‐catalyzed intramolecular hydroamination of allenylamines (Scheme ),58 as well as the cyclization of 2,3‐allenamides with CuBr 2 have been described 59. Allenes with γ‐sulfonamide substituents have been cyclized to pyrrolidines with high trans selectivity using an acylcobalt reagent 60…”